The Eastern Shore Hotels


Great Oak Manor

At a Glance


  • stunning waterside location


  • formal period decor may be stuffy
  • cancellations must be made 14 days prior to arrival
  • cell phone coverage is spotty

Great Oak Manor Review

On 12 acres sloping gently to a gazebo on the edge of its private Chesapeake beach, this stately 18th-century Georgian brick manor house provides a taste of Eastern Shore gentility. Its antique furnishings and Oriental rugs, along with an airy sunporch, re-create a bygone era. Of its 11 impeccably decorated guest rooms, five have working fireplaces. The manor's formal library is well stocked with both books and films. If needed, guests are provided transportation to the restaurant of their choice for dinner. Golf and tennis are available at neighboring Great Oak Landing.

    Contact Information

  • Address: 10568 Cliff Rd., Chestertown, MD, 21620-4115 | Map It
  • Phone: 410/778–5943; 877/502–6892
  • Website:
  • Location: Chestertown

    Hotel Details

  • 11 rooms
  • Rate includes breakfast.
  • Credit cards accepted.

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